Methyl chloroformate → 3-Hydroxy-2-(hydroxymethyl)propyl methyl carbonate

HRID 1594623Notes

Reaction equation

HRID 1594623 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].Cl[C:9]([O:11][CH3:12])=[O:10]>ClCCl.N1C=CC=CC=1>[CH3:12][O:11][C:9]([O:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5])=[O:10]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 78432Trimethylolmethane

Product 1

HCID 222749913-Hydroxy-2-(hydroxymethyl)propyl methyl carbonateYield 42.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(hydroxymethyl)-1,3-propanediol (9.4 mmol) in dichloromethane (20 mL) and pyridine (7.5 mL) at 0° C. was added methyl chloroformate (9.4 mmol) slowly. The resulting solution was warmed to room temperature and stirred for 16 h. The reaction was concentrated under reduced pressure and chromatographed by eluting with methanol-dichloromethane (1:4) to give 650 mg of 2-(methoxycarbonyloxymethyl)-1,3-propanediol.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customchromatographed
  3. washby eluting with methanol-dichloromethane (1:4)

Sources & evidence

ORD record
ord-229c0332f800471186e76169b9bd5975
Source dataset
uspto-grants-2001_09
Patent number
US06284748B1

Reaction notes

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